For a quarter-century, Trump has played a prominent role in the McMahons' professional wrestling empire. He has hosted events at his venues and appeared in the ring. In 2013, he earned membership in the WWE Hall of Fame. However, this is not the first time Trump's unconventional brand of politics has been at odds with what otherwise has been a lucrative relationship.

In 2012, when Linda McMahon was running for a U.S. Senate seat, her campaign attempted to deny she had donated to Trump's charity in a move to distance her from the Obama "birther" theory Trump was trumpeting at the time.

Nevertheless, in the 2014 cycle, the McMahons showed a willingness to spread their wealth around, donating millions of dollars to various GOP candidates, party committees, and super PACs. A super PAC has been formed to support Trump, however the billionaire has signaled he is willing to finance his own White House run.